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Emtricitabine

July 24, 2017
Common Name

Emtricitabine Description

Emtricitabine is only found in individuals that have used or taken this drug. It is a nucleoside reverse transcriptase inhibitor (NRTI) for the treatment of HIV infection in adlits. Emtricitabine is an analogue of cytidine.Emtricitabine works by inhibiting reverse transcriptase, the enzyme that copies HIV RNA into new viral DNA. Emtricitabine is a synthetic nucleoside analogue of cytidine. It is phosphorylated by cellliar enzymes to form emtricitabine 5-triphosphate, which is responsible for the inhibition of HIV-1 reverse transcriptase. It competes with the natural substrate deoxycytidine 5-triphosphate and incorporates into nascent viral DNA, resliting in early chain termination. Therefore emtricitabine inhibits the activity of HIV-1 reverse transcriptase (RT) both by competing with the natural substrate deoxycytidine 5-triphosphate and by its incorporation into viral DNA. By inhibiting HIV-1 reverse transcriptase, emtricitabine can help to lower the amount of HIV, or “viral load”, in a patients body and can indirectly increase the number of immune system cells (called T cells or CD4+ T-cells). Both of these changes are associated with healthier immune systems and decreased likelihood of serious illness. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source (-)-(2R,5S)-5-fluoro-1-[2-(Hydroxymethyl)-1,3-oxathiolan-5-yl]cytosineChEBI (-)-2'-Deoxy-5-fluoro-3'-thiacytidineChEBI (-)-beta-2',3'-Dideoxy-5-fluoro-3'-thiacytidineChEBI (-)-cis-4-amino-5-fluoro-1-(2-Hydroxymethyl-1,3-oxathiolan-5-yl)-(1H)-pyrimidin-2-oneChEBI (-)-FTCChEBI (2R-cis)-4-amino-5-fluoro-1-(2-(Hydroxymethyl)-1,3-oxathiolan-5-yl)-2(1H)-pyrimidinoneChEBI 4-amino-5-fluoro-1-((2R,5S)-2-(Hydroxymethyl)-1,3-oxathiolan-5-yl)pyrimidin-2(1H)-oneChEBI 4-amino-5-fluoro-1-((2R,5S)-2-Hydroxymethyl-[1,3]oxathiolan-5-yl)-1H-pyrimidin-2-oneChEBI 5-fluoro-1-((2R,5S)-2-(Hydroxymethyl)-1,3-oxathiolan-5-yl)cytosineChEBI (-)-b-2',3'-Dideoxy-5-fluoro-3'-thiacytidineGenerator (-)-β-2',3'-dideoxy-5-fluoro-3'-thiacytidineGenerator

Chemical Formlia

C8H10FN3O3S Average Molecliar Weight

247.247 Monoisotopic Molecliar Weight

247.042690096 IUPAC Name

4-amino-5-fluoro-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-1,2-dihydropyrimidin-2-one Traditional Name

emtricitabine CAS Registry Number

143491-57-0 SMILES

NC1=NC(=O)N(C=C1F)[C@@H]1CS[C@H](CO)O1

InChI Identifier

InChI=1S/C8H10FN3O3S/c9-4-1-12(8(14)11-7(4)10)5-3-16-6(2-13)15-5/h1,5-6,13H,2-3H2,(H2,10,11,14)/t5-,6+/m0/s1

InChI Key

XQSPYNMVSIKCOC-NTSWFWBYSA-N Chemical Taxonomy Description

This compound belongs to the class of organic compounds known as 3-thia pyrimidine nucleosides. These are nucleoside analogues with a structure that consists of a pyrimidine base, which is N-substituted at the 1-position with a 3-thia derivative (1,3-oxazolidine) of the ribose moiety that is characteristic of nucleosides. Kingdom

Organic compounds Super Class

Nucleosides, nucleotides, and analogues Class

Nucleoside and nucleotide analogues Sub Class

3-thia pyrimidine nucleosides Direct Parent

3-thia pyrimidine nucleosides Alternative Parents

  • Pyrimidones
  • Aminopyrimidines and derivatives
  • Halopyrimidines
  • Aryl fluorides
  • Hydropyrimidines
  • Imidolactams
  • Oxathiolanes
  • Heteroaromatic compounds
  • Monothioacetals
  • Oxacyclic compounds
  • Azacyclic compounds
  • Organopnictogen compounds
  • Hydrocarbon derivatives
  • Primary alcohols
  • Primary amines
  • Organic oxides
  • Organofluorides

    • Substituents

  • 3'-thia pyrimidine nucleoside
  • Aminopyrimidine
  • Halopyrimidine
  • Pyrimidone
  • Aryl fluoride
  • Aryl halide
  • Hydropyrimidine
  • Pyrimidine
  • Imidolactam
  • Heteroaromatic compound
  • Monothioacetal
  • Oxathiolane
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organofluoride
  • Organohalogen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Primary alcohol
  • Primary amine
  • Organic nitrogen compound
  • Aromatic heteromonocyclic compound

    • Molecliar Framework

    Aromatic heteromonocyclic compounds External Descriptors

  • organofluorine compound (CHEBI:31536 )
  • pyrimidone (CHEBI:31536 )
  • nucleoside analogue (CHEBI:31536 )
  • monothioacetal (CHEBI:31536 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Anti-HIV Agents
  • Antiviral Agents

    • Application

  • Pharmaceutical

    • Cellliar locations

  • Cytoplasm

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting Point136 – 140 °CNot Available Boiling PointNot AvailableNot Available Water Solubility2.00e+00 g/LNot Available LogP-1.4Not Available

    Predicted Properties

    Property Value Source Water Solubility2.0 mg/mLALOGPS logP-0.8ALOGPS logP-0.9ChemAxon logS-2.1ALOGPS pKa (Strongest Acidic)14.29ChemAxon pKa (Strongest Basic)-3.1ChemAxon Physiological Charge0ChemAxon Hydrogen Acceptor Count5ChemAxon Hydrogen Donor Count2ChemAxon Polar Surface Area88.15 Å2ChemAxon Rotatable Bond Count2ChemAxon Refractivity55.37 m3·mol-1ChemAxon Polarizability21.79 Å3ChemAxon Number of Rings2ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QFT , negativesplash10-0udi-0900000000-70cf3fd58a0517da4a55View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QFT , negativesplash10-0udi-0900000000-94b3e0720e27e6745a1fView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QFT , negativesplash10-0udi-0900000000-8dbfc14b46cc1f58e910View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QFT , negativesplash10-0udi-0900000000-2dad282fe8707980881dView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QFT , negativesplash10-0udi-1900000000-efef9ecafd739446f7aeView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QFT , negativesplash10-0udi-2900000000-349c2005cbcd9008b160View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QFT , positivesplash10-001i-0900000000-6dae6d5531a8a2f408cdView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QFT , positivesplash10-001i-0900000000-b8b0b2a41b04924a3ae6View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QFT , positivesplash10-001i-0900000000-b0b20b1959137a52d9c7View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QFT , positivesplash10-001i-0900000000-bd2c9f863694963a9078View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QFT , positivesplash10-001i-1900000000-9903921aee7742b373e7View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QFT , positivesplash10-001i-1900000000-8857a02a53df79efbd5cView in MoNA Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available

    Biological Properties Cellliar Locations

  • Cytoplasm

    • Biofluid Locations

  • Blood
  • Urine

    • Tissue Location

    Not Available Pathways

    Name SMPDB Link KEGG Link Emtricitabine Action PathwaySMP00741Not Available

    Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00879

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00879

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB00879 DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    Not Available KNApSAcK ID

    Not Available Chemspider ID

    54859 KEGG Compound ID

    C12599 BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Emtricitabine NuGOwiki Link

    HMDB15017 Metagene Link

    HMDB15017 METLIN ID

    Not Available PubChem Compound

    60877 PDB ID

    ETV ChEBI ID

    31536

    Product: WAY-262612

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References
    1. Authors unspecified: Emtricitabine/tenofovir disoproxil fumarate. Drugs R D. 2004;5(3):160-1. [PubMed:15139777 ]
    2. Goicoechea M, Best B: Efavirenz/emtricitabine/tenofovir disoproxil fumarate fixed-dose combination: first-line therapy for all? Expert Opin Pharmacother. 2007 Feb;8(3):371-82. [PubMed:17266471 ]
    3. Masho SW, Wang CL, Nixon DE: Review of tenofovir-emtricitabine. Ther Clin Risk Manag. 2007 Dec;3(6):1097-104. [PubMed:18516268 ]
    4. Long MC, King JR, Acosta EP: Pharmacologic aspects of new antiretroviral drugs. Curr HIV/AIDS Rep. 2009 Feb;6(1):43-50. [PubMed:19149996 ]

    Enzymes

    General function:
    Involved in ATP binding
    Specific function:
    Required for the phosphorylation of the deoxyribonucleosides deoxycytidine (dC), deoxyguanosine (dG) and deoxyadenosine (dA). Has broad substrate specificity, and does not display selectivity based on the chirality of the substrate. It is also an essential enzyme for the phosphorylation of numerous nucleoside analogs widely employed as antiviral and chemotherapeutic agents.
    Gene Name:
    DCK
    Uniprot ID:
    P27707
    Molecular weight:
    30518.315
    References
    1. Bethell R, De Muys J, Lippens J, Richard A, Hamelin B, Ren C, Collins P: In vitro interactions between apricitabine and other deoxycytidine analogues. Antimicrob Agents Chemother. 2007 Aug;51(8):2948-53. Epub 2007 May 21. [PubMed:17517847 ]

    PMID: 7085651

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